2,4-Dihydroxybenzaldehyde → HCID 86713214, compound

HRID 1056814Notes

Reaction equation

HRID 1056814 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(#N)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 23393Picolyl chloride

Product 1

HCID 86713214HCID 86713214, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Separately, 13.8 g (100 mmol) of 2,4-dihydroxybenzaldehyde was dissolved in 250 mL of acetonitrile and 32.5 g (100 mmol) of cesium carbonate was added at room temperature. To this solution, the solution of 2-chloromethylpyridine in acetonitrile prepared in advance was added dropwise at 50° C. over 4 hours and the mixture was stirred for 11 hours. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50) to give 6.10 g (27% yield) of the title compound as a white solid.

Workup

  1. additionwas added dropwise at 50° C. over 4 hours
  2. filtrationAfter filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50)

Sources & evidence

ORD record
ord-c43361e4338d4914b96298f2a8b738bb
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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